Should I message him?

So i think this guy is cute and i had a crush on him in high school and i follow him on instagram and i want to DM him and just say i think he has a cute smile (which he does) but he hasn't posted a pic on instagram in about 2 weeks i guess. I never spoke to him in high school cuz i was too shy but im tired of wondering if i have a chance. So should i have some courage and DM him?